Controllable synthesis of a large TS-1 catalyst for clean epoxidation of a C=C double bond under mild conditions

doi:10.1007/s11705-022-2280-x

Front. Chem. Sci. Eng.

2023, Vol. 17

Issue (6) : 772-783 https://doi.org/10.1007/s11705-022-2280-x

RESEARCH ARTICLE

Controllable synthesis of a large TS-1 catalyst for clean epoxidation of a C=C double bond under mild conditions

Xiu Gao^1,², Beining Luo^1,², Yanping Hong^1,², Peihang He^1,², Zedong Zhang^1,², Guoqiang Wu^1,²(

)

¹. Jiangxi Key Laboratory of Natural Products and Functional Food, Jiangxi Agricultural University, Nanchang 330045, China
². School of Food Science and Engineering, Jiangxi Agricultural University, Nanchang 330045, China

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Abstract

Development of a titanium silicalite-1 (TS-1) catalyst with good crystallinity and a four-coordinate Ti framework is critical for efficient catalytic oxidation reaction under mild conditions. Herein, a size-controlled TS-1 zeolite (TS-1 0.1ACh (acetylcholine)) was synthesized via steam-assisted crystallization by introducing acetylcholine as a crystal growth modifier in the preparation process, and TS-1 0.1ACh was also employed in epoxidations of different substrates containing C=C double bonds. The crystalline sizes of the as-synthesized TS-1 0.1ACh catalysts were controlled with the acetylcholine content, and characterization results showed that the particle sizes of highly crystalline TS-1 0.1ACh zeolite reached 3.0 μm with a good Ti framework. Throughout the synthetic process, the growth rate of the crystals was accelerated by electrostatic interactions between the connected hydroxyl groups of the acetylcholine modifier and the negatively charged skeleton of the pre-zeolites. Furthermore, the TS-1 0.1ACh catalyst demonstrated maximum catalytic activity, good selectivity and high stability during epoxidation of allyl chloride. Importantly, the TS-1 0.1ACh catalyst was also highly versatile and effective with different unsaturated substrates. These findings may provide novel, easily separable and large TS-1 catalysts for efficient and clean industrial epoxidations of C=C double bonds.

Keywords size-controlled TS-1 crystal modifier steam-assisted crystallization epoxidation

Corresponding Author(s): Guoqiang Wu

Online First Date: 31 March 2023 Issue Date: 17 May 2023

Cite this article:

Xiu Gao,Beining Luo,Yanping Hong, et al. Controllable synthesis of a large TS-1 catalyst for clean epoxidation of a C=C double bond under mild conditions[J]. Front. Chem. Sci. Eng., 2023, 17(6): 772-783.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-022-2280-x
https://academic.hep.com.cn/fcse/EN/Y2023/V17/I6/772

Fig.1 XRD diffraction patterns of the TS-1-s and TS-1#xACh: (a) 2θ = 5°–80°; (b) 2θ = 20°–25°.

Tab.1 Specific surface areas, crystallinities and crystal size of all samples

Fig.2 SEM images of (a) TS-1-s, (b) TS-1#0.05ACh, (c) TS-1#0.075ACh, (d–f) TS-1#0.1ACh, (g) TS-1#0.2ACh and (h) TS-1#0.4ACh.

Fig.3 TEM images of (a) TS-1-s, (b–d) TS-1#0.1ACh; (e) HAADF-STEM image of TS-1#0.1ACh, and (f–h) elemental maps for O, Si and Ti in TS-1#0.1ACh.

Fig.4 (a) Nitrogen physisorption curves and (b) UV–vis spectra for TS-1-s and TS-1#xACh; XPS (c) Ti 2p spectra of TS-1#0.1ACh and (d) O 1s spectra of TS-1#0.1ACh.

Fig.5 XRD patterns for the TS-1#0.1ACh crystallized at 170 °C for different times.

Fig.6 SEM images of TS-1#0.1ACh crystallized at 170 °C for different times: (a) 4 h, (b) 8 h, (c) 13 h, and (d) 18 h.

Scheme1 Proposed synthetic process for large TS-1 zeolites via introduction of an acetylcholine modifier into the steam-assisted crystallization system.

Fig.7 ACH conversion, H₂O₂ conversion and ECH selectivity of TS-1-s and TS-1#xACh catalysts (reaction conditions: C=C:H₂O₂ = 2:3 (molar ratio), 3.4 g of H₂O₂, 0.1 g of catalyst, 20 mL of methanol, 60 °C, 4 h).

Fig.8 Recycling and regeneration of TS-1#0.1ACh in ACH epoxidation (reaction conditions: C=C:H₂O₂ = 2:3 (molar ratio), 3.4 g of H₂O₂, 0.1 g of catalyst, 20 mL of methanol, 60 °C, 4 h).

Tab.2 Epoxidation of various monoalkenes and methyl oleate catalyzed by TS-1#0.1ACh

1	J Li, X Meng, F S Xiao. Zeolites for control of NO emissions: opportunities and challenges. Chem Catalysis, 2022, 2(2): 253–261 https://doi.org/10.1016/j.checat.2021.11.011
2	Q Zhang, J Yu, A Corma. Applications of zeolites to C1 chemistry: recent advances, challenges, and opportunities. Advanced Materials, 2020, 32(44): e2002927 https://doi.org/10.1002/adma.202002927
3	C Martínez, A Corma. Inorganic molecular sieves: preparation, modification and industrial application in catalytic processes. Coordination Chemistry Reviews, 2011, 255(13–14): 1558–1580 https://doi.org/10.1016/j.ccr.2011.03.014
4	Y Li, L Li, J Yu. Applications of zeolites in sustainable chemistry. Chem, 2017, 3(6): 928–949 https://doi.org/10.1016/j.chempr.2017.10.009
5	J Wang, J Jiang, J Ding, X Wang, Y Sun, R Ruan, A J Ragauskas, Y S Ok, D C W Tsang. Promoting Diels-Alder reactions to produce bio-BTX: co-aromatization of textile waste and plastic waste over USY zeolite. Journal of Cleaner Production, 2021, 314: 127966 https://doi.org/10.1016/j.jclepro.2021.127966
6	T Odedairo, S Al-Khattaf. Comparative study of zeolite catalyzed alkylation of benzene with alcohols of different chain length: H-ZSM-5 versus mordenite. Catalysis Today, 2013, 204: 73–84 https://doi.org/10.1016/j.cattod.2012.05.052
7	Y Xie, M Wang, X Wang, L Wang, P Ning, Y Ma, J Lu, R Cao, Y Xue. Magnetic-field-assisted catalytic oxidation of arsine over Fe/HZSM-5 catalyst: synergistic effect of Fe species and activated surface oxygen. Journal of Cleaner Production, 2022, 337: 130549 https://doi.org/10.1016/j.jclepro.2022.130549
8	M TaramassoG PeregoB Notari. Preparation of porous crystalline synthetic materials comprised of silicon and titanium oxide. US Patent, 4410501, 1983
9	G Wu, Z Lin, L Li, L Zhang, Y Hong, W Wang, C Chen, Y Jiang, X Yan. Experiments and kinetics of the epoxidation of allyl chloride with H2O2 over organic base treated TS-1 catalysts. Chemical Engineering Journal, 2017, 320: 1–10 https://doi.org/10.1016/j.cej.2017.03.030
10	I Khan, X Chu, Y Liu, S Khan, L Bai, L Jing. Synthesis of Ni2+ cation modified TS-1 molecular sieve nanosheets as effective photocatalysts for alcohol oxidation and pollutant degradation. Chinese Journal of Catalysis, 2020, 41(10): 1589–1602 https://doi.org/10.1016/S1872-2067(20)63555-0
11	P Yao, Y Wang, T Zhang, S Wang, X Wu. Effect of sodium ions in synthesis of titanium silicalite-1 on its catalytic performance for cyclohexanone ammoximation. Frontiers of Chemical Science and Engineering, 2014, 8(2): 149–155 https://doi.org/10.1007/s11705-014-1409-y
12	C P Gordon, H Engler, A S Tragl, M Plodinec, T Lunkenbein, A Berkessel, J H Teles, A N Parvulescu, C Coperet. Efficient epoxidation over dinuclear sites in titanium silicalite-1. Nature, 2020, 586(7831): 708–713 https://doi.org/10.1038/s41586-020-2826-3
13	N Wilde, M Pelz, S G Gebhardt, R Gläser. Highly efficient nano-sized TS-1 with micro-/mesoporosity from desilication and recrystallization for the epoxidation of biodiesel with H2O2. Green Chemistry, 2015, 17(6): 3378–3389 https://doi.org/10.1039/C5GC00406C
14	N Wilde, J Přech, M Pelz, M Kubů, J Čejka, R Gläser. Accessibility enhancement of TS-1-based catalysts for improving the epoxidation of plant oil-derived substrates. Catalysis Science & Technology, 2016, 6(19): 7280–7288 https://doi.org/10.1039/C6CY01232A
15	X Feng, D Lin, D Chen, C Yang. Rationally constructed Ti sites of TS-1 for epoxidation reactions. Science Bulletin, 2021, 66(19): 1945–1949 https://doi.org/10.1016/j.scib.2021.05.020
16	Z Yang, R Zhang, R Liu, S Zhang. Elucidating the zeolite particle size effect on butene/isobutane alkylation. Industrial & Engineering Chemistry Research, 2022, 61(2): 1032–1043 https://doi.org/10.1021/acs.iecr.1c02038
17	Q Wu, C Xu, L Zhu, X Meng, F S Xiao. Recent strategies for synthesis of metallosilicate zeolites. Catalysis Today, 2022, 390-391: 2–11 https://doi.org/10.1016/j.cattod.2022.01.020
18	P Lanzafame, G Papanikolaou, K Barbera, G Centi, S Perathoner. Etherification of HMF to biodiesel additives: the role of NH4+ confinement in Beta zeolites. Journal of Energy Chemistry, 2019, 36: 114–121 https://doi.org/10.1016/j.jechem.2019.07.009
19	J Ungula, H C Swart. Controlling the morphology of ZnO NRs grown on GZO seed layer, by use of ethylenediamine and L-cysteine as crystal growth modifiers and complexing agents. Applied Surface Science, 2019, 487: 1198–1208 https://doi.org/10.1016/j.apsusc.2019.05.194
20	J Lu, Q Li, W Song, Z Liu, C Wang. The influence of crystal modifiers on the crystallinity, particle morphology and brightness of precipitated calcite powders hydrothermally prepared from black marble waste. Powder Technology, 2020, 373: 535–542 https://doi.org/10.1016/j.powtec.2020.07.002
21	W Ma, J F Lutsko, J D Rimer, P G Vekilov. Antagonistic cooperativity between crystal growth modifiers. Nature, 2020, 577(7791): 497–501 https://doi.org/10.1038/s41586-019-1918-4
22	F Jones, M I Ogden. Controlling crystal growth with modifiers. CrystEngComm, 2010, 12(4): 1016–1023 https://doi.org/10.1039/B918849E
23	M Li, X Shen, M Liu, J Lu. Synthesis TS-1 nanozelites via L-lysine assisted route for hydroxylation of benzene. Molecular Catalysis, 2021, 513: 111779 https://doi.org/10.1016/j.mcat.2021.111779
24	X Song, X Yang, T Zhang, H Zhang, Q Zhang, D Hu, X Chang, Y Li, Z Chen, M Jia, P Zhang, J Yu. Controlling the morphology and titanium coordination states of TS-1 zeolites by crystal growth modifier. Inorganic Chemistry, 2020, 59(18): 13201–13210 https://doi.org/10.1021/acs.inorgchem.0c01518
25	J Zhang, S Bai, Z Chen, Y Wang, L Dong, H Zheng, F Cai, M Hong. Core-shell zeolite Y with ant-nest like hollow interior constructed by amino acids and enhanced catalytic activity. Journal of Materials Chemistry A: Materials for Energy and Sustainability, 2017, 5(39): 20757–20764 https://doi.org/10.1039/C7TA05048H
26	Q Zhang, A Mayoral, O Terasaki, Q Zhang, B Ma, C Zhao, G Yang, J Yu. Amino acid-assisted construction of single-crystalline hierarchical nanozeolites via oriented-aggregation and intraparticle ripening. Journal of the American Chemical Society, 2019, 141(9): 3772–3776 https://doi.org/10.1021/jacs.8b11734
27	C Yang, Z Dong, W Chu, Y Wang, D Zhao, F Chen, W Xin, X Zhu, S Liu, L Xu. Understanding the roles of different acid sites in beta zeolites with different particle sizes catalyzed liquid-phase transalkylation of diethylbenzene with benzene. Catalysis Science & Technology, 2022, 12(2): 652–663 https://doi.org/10.1039/D1CY01849C
28	C Chen, L Cai, L Li, L Bao, Z Lin, G Wu. Heterogeneous and non-acid process for production of epoxidized soybean oil from soybean oil using hydrogen peroxide as clean oxidant over TS-1 catalysts. Microporous and Mesoporous Materials, 2019, 276: 89–97 https://doi.org/10.1016/j.micromeso.2018.09.028
29	Bocanegra N Ramírez, Vázquez S I Suarez, Rangel L Sandoval, Navarro M A Garza, de la Rosa J Rivera, Ortiz C J Lucio, G A Flores-Escamilla, López I A Santos, Pedraza E S Carrillo, Sánchez M Bravo, Haro Del Río D A De. Catalytic conversion of GVL to biofuels using Cu and Pt catalysts over microwave-synthesized FAU zeolite. Catalysis Today, 2022, 392-393: 105–115 https://doi.org/10.1016/j.cattod.2021.06.026
30	K Ueno, S Yamada, H Negishi, T Okuno, H Tawarayama, S Ishikawa, M Miyamoto, S Uemiya, Y Oumi. Fabrication of pure-silica *BEA-type zeolite membranes on tubular silica supports coated with dilute synthesis gel via steam-assisted conversion. Separation and Purification Technology, 2020, 247: 116934 https://doi.org/10.1016/j.seppur.2020.116934
31	M Liu, Z Chang, H Wei, B Li, X Wang, Y Wen. Low-cost synthesis of size-controlled TS-1 by using suspended seeds: from screening to scale-up. Applied Catalysis A: General, 2016, 525: 59–67 https://doi.org/10.1016/j.apcata.2016.07.006
32	W Xu, T Zhang, R Bai, P Zhang, J Yu. A one-step rapid synthesis of TS-1 zeolites with highly catalytically active mononuclear TiO6 species. Journal of Materials Chemistry A: Materials for Energy and Sustainability, 2020, 8(19): 9677–9683 https://doi.org/10.1039/C9TA13851J
33	X Gao, Y Zhang, Y Hong, B Luo, X Yan, G Wu. Efficient and clean epoxidation of methyl oleate to epoxidized methyl oleate catalyzed by external surface of TS-1 supported molybdenum catalysts. Microporous and Mesoporous Materials, 2022, 333: 111731 https://doi.org/10.1016/j.micromeso.2022.111731
34	L Cai, C Chen, W Wang, X Gao, X Kuang, Y Jiang, L Li, G Wu. Acid-free epoxidation of soybean oil with hydrogen peroxide to epoxidized soybean oil over titanium silicalite-1 zeolite supported cadmium catalysts. Journal of Industrial and Engineering Chemistry, 2020, 91: 191–200 https://doi.org/10.1016/j.jiec.2020.07.052
35	X Li, X Yang, Q Wang, S Li, Y Ye, D Wang, Z Zheng. Synthesis of Pt-based TS-1 catalysts for selective hydrogenation to produce C15–C18 alkanes from the FAME: effect of rare-earth metal additives. Journal of Cleaner Production, 2022, 350: 131520 https://doi.org/10.1016/j.jclepro.2022.131520
36	J Xu, Y Wang, W Feng, Y Lin, S Wang. Effect of triethylamine treatment of titanium silicalite-1 on propylene epoxidation. Frontiers of Chemical Science and Engineering, 2014, 8(4): 478–487 https://doi.org/10.1007/s11705-014-1453-7
37	Z Di, H Chen, R Zhang, H Wang, J Jia, Y Wei. Significant promotion of reducing treatment on Pd/TS-1 zeolite for formaldehyde catalytic purification at ambient temperature. Applied Catalysis B: Environmental, 2022, 304: 120843 https://doi.org/10.1016/j.apcatb.2021.120843
38	Z Chen, J Zhang, B Yu, G Zheng, J Zhao, M Hong. Amino acid mediated mesopore formation in LTA zeolites. Journal of Materials Chemistry A: Materials for Energy and Sustainability, 2016, 4(6): 2305–2313 https://doi.org/10.1039/C5TA09860B
39	A Thangaraj, M J Eapen, S Sivasanker, P Ratnasamy. Studies on the synthesis of titanium silicalite, TS-1. Zeolites, 1992, 12(8): 943–950 https://doi.org/10.1016/0144-2449(92)90159-M
40	A Wróblewska, J Tołpa, D Kłosin, P Miądlicki, Z C Koren, B Michalkiewicz. The application of TS-1 materials with different titanium contents as catalysts for the autoxidation of α-pinene. Microporous and Mesoporous Materials, 2020, 305: 110384 https://doi.org/10.1016/j.micromeso.2020.110384
41	H Yin, F Su, C Luo, L Zhu, W Zhong, L Mao, K You, D Yin. Visible-light-mediated remote aliphatic C–H oxyfunctionalization over CuCl2 decorated hollowed-TS-1 photocatalysts. Applied Catalysis B: Environmental, 2022, 302: 120851 https://doi.org/10.1016/j.apcatb.2021.120851
42	Z Zhang, G P Cao, Q Cai, H Lu, S Ji, R Fang, P Gao, M Feng. Steam-assisted in situ prepared TS-1 with hierarchical pores and tunable acid sites grown on carbon nanotubes decorated nickel foam. Industrial & Engineering Chemistry Research, 2020, 59(7): 2761–2772 https://doi.org/10.1021/acs.iecr.9b06065
43	Z Song, J Yuan, Z Cai, D Lin, X Feng, N Sheng, Y Liu, X Chen, X Jin, D Chen, C Yang. Engineering three-layer core−shell S-1/TS-1@dendritic-SiO2 supported Au catalysts towards improved performance for propene epoxidation with H2 and O2. Green Energy & Environment, 2020, 5(4): 473–483 https://doi.org/10.1016/j.gee.2020.11.017
44	Y Wei, G Li, Q Lü, C Cheng, H Guo. Green and efficient epoxidation of methyl oleate over hierarchical TS-1. Chinese Journal of Catalysis, 2018, 39(5): 964–972 https://doi.org/10.1016/S1872-2067(18)63014-1
45	Y Sun, G Li, Y Gong, Z Sun, H Yao, X Zhou. Ag and TiO2 nanoparticles co-modified defective zeolite TS-1 for improved photocatalytic CO2 reduction. Journal of Hazardous Materials, 2021, 403: 124019 https://doi.org/10.1016/j.jhazmat.2020.124019
46	W Sun, H Song, Z Xi, J Ma, B Wang, X Liu, C Hao, K Chen. Synthesis and enhanced electrorheological properties of TS-1/titanium oxide core/shell nanocomposite. Industrial & Engineering Chemistry Research, 2020, 59(3): 1168–1182 https://doi.org/10.1021/acs.iecr.9b05936
47	O V Kazarina, V N Agieienko, R N Nagrimanov, M E Atlaskina, A N Petukhov, A A Moskvichev, A V Nyuchev, A V Barykin, I V Vorotyntsev. A rational synthetic approach for producing quaternary ammonium halides and physical properties of the room temperature ionic liquids obtained by this way. Journal of Molecular Liquids, 2021, 344: 117925 https://doi.org/10.1016/j.molliq.2021.117925
48	Q Zhang, G Chen, Y Wang, M Chen, G Guo, J Shi, J Luo, J Yu. High-quality single-crystalline MFI-type nanozeolites: a facile synthetic strategy and MTP catalytic studies. Chemistry of Materials, 2018, 30(8): 2750–2758 https://doi.org/10.1021/acs.chemmater.8b00527
49	D Guo, J Lai, F Cheng, W Zhao, H Chen, H Li, X Liu, D Yin, N Yu. Titanium silicalite-1 supported bimetallic catalysts for selective hydrogenolysis of 5-hydroxymethylfurfural to biofuel 2,5-dimethylfuran. Chemical Engineering Journal Advances, 2021, 5: 100081 https://doi.org/10.1016/j.ceja.2020.100081
50	J Zhuang, D Ma, Z Yan, X Liu, X Han, X Bao, Y Zhang, X Guo, X Wang. Effect of acidity in TS-1 zeolites on product distribution of the styrene oxidation reaction. Applied Catalysis A: General, 2004, 258(1): 1–6 https://doi.org/10.1016/j.apcata.2003.06.002
51	Y Wei, G Li, C Wang, H Guo. Integrated fast-mass transfer and high Ti-sites utilization into hybrid amphiphilic TS@PMO catalyst towards efficient solvent-free methyl oleate epoxidation. Journal of Colloid and Interface Science, 2021, 586: 233–242 https://doi.org/10.1016/j.jcis.2020.10.087
52	Y Nakagawa, K Kamata, M Kotani, K Yamaguchi, N Mizuno. Polyoxovanadometalate-catalyzed selective epoxidation of alkenes with hydrogen peroxide. Angewandte Chemie International Edition, 2005, 44(32): 5136–5141 https://doi.org/10.1002/anie.200500491
53	S Bhattacharya, N Kumari. Metallomicelles as potent catalysts for the ester hydrolysis reactions in water. Coordination Chemistry Reviews, 2009, 253(17-18): 2133–2149 https://doi.org/10.1016/j.ccr.2009.01.016

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